Make the dough: Add the yeast to the lukewarm water. Stir and let stand 5 minutes. Combine the dry ingredients in a large bowl or the bowl of a stand mixer. Add the warmed milk, vegetable oil and yeast mixture. Knead with the dough hook until dough is smooth, adding more flour a Tablespoon at a time, as necessary, until you have a smooth, moist dough. Remove dough to an oiled bowl, cover with plastic wrap and let rise to doubled, about 60 minutes.
Grease a skillet and set aside. (My skillet is 8" bottom diameter and 10" top diameter. Anything of a similar size will work).
Divide dough into two pieces and roll into a rope about 3 feet long. Place the dough on to a long piece or parchment or foil wrap and liberally brush with melted butter mixed with the vanilla. Pour the brown sugar/cinnamon mixture evenly alongside the buttered ropes and then roll the ropes in the mixture until evenly covered. Pinch the end of the ropes together and then twist them together, pinching the other end once all twisted together.
Place twisted ropes into the skillet, starting from the centre and winding it around. (If you have some melted butter left over from brushing, feel free to drizzle it over the dough). Cover the skillet with greased plastic wrap and let rise until doubled.
Meanwhile, prepare the streusel topping by combining dry ingredients and cutting in the cold butter with a fork. Set aside.
Preheat oven to 350° F. Once dough is doubled, sprinkle with streusel topping and bake for for 40-45 minutes, covering it with foil after 25 or 30 minutes if is dark enough.
Meanwhile, prepare the glaze by combining the wet ingredients and adding to the powdered sugar. Stir well until smooth. Pour evenly over bread once it has cooled a bit.
Notes
Overnight Rise Option: Prepare through to placing the bread into the skillet, then cover tightly with plastic wrap and refrigerate overnight. Remove from the fridge in the morning, preheat the oven and bake.